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Pyridinium Ylide-Mediated Diastereoselective Synthesis of Spirocyclopropanyl-pyrazolones via Cascade Michael/Substitution Reaction
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2024-05-14 , DOI: 10.1021/acs.joc.3c02879
Akanksha Kumari 1 , Dhirajkumar Jitendrabhai Patanvadiya 1 , Anshul Jain 1 , Ranjan Patra 2 , Manikandan Paranjothy 1 , Nirmal K. Rana 1
Affiliation  

We have devised a highly diastereoselective formal [2 + 1] annulation reaction of arylidene/alkylidine-pyrazolones with in situ-generated supported as well as standard pyridinium ylides to construct spirocyclopropanyl-pyrazolones. The cascade approach exhibits a wide range of functional group tolerance, gram-scale capability, and substrate versatility. A diverse range of spirocyclic cyclopropanes was synthesized extensively with both mediators, and the supported pyridine was reused in subsequent cycles. Density functional theory calculations confirmed the formation of spirocyclopropane as the lower energy pathway.

中文翻译:

吡啶叶立德介导的级联迈克尔/取代反应非对映选择性合成螺环丙基吡唑啉酮

我们设计了亚芳基/亚烷基-吡唑啉酮与原位生成的负载吡啶鎓叶立德以及标准吡啶鎓叶立德的高度非对映选择性形式[2 + 1]成环反应,以构建螺环丙基-吡唑啉酮。级联方法表现出广泛的官能团耐受性、克级能力和底物多功能性。用两种介体广泛合成了多种螺环环丙烷,并且负载的吡啶在后续循环中重复使用。密度泛函理论计算证实了螺环丙烷的形成是较低能量的途径。
更新日期:2024-05-14
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